Heather McDonald Dating Advice

Comedienne and Author Heather McDonald Gives Valentine's Day Advice

From blue balls to babies, Chelsea Lately writer and comedienne Heather McDonald followed up her book You'll Never Blue Ball in This Town Again — about losing her virginity at 27 — with My Inappropriate Life, which came out last week. Her latest memoir is a hilarious look at her "grown-up" life with a husband and three kids, which includes a lot of Real Housewives references, Chardonnay, and stories about balancing family life with her career. We recently chatted with Heather about Valentine's Day, and she gave some helpful advice on the holiday along with sharing a V-Day horror story. She also answered some burning reader questions from our Group Therapy community group. Get her dating words of wisdom now!

POPSUGAR: Do you have any Valentine's Day advice for single women who hate the holiday?Heather McDonald: It is on a Thursday night, which is nice, this year. If you have a couple single girlfriends, I do think it can be fun. It's just either get together or stay in. Some people go out, a bar or something, but I wouldn't want to do that. I think that would depress me. But getting together with some girlfriends and just having a dinner somewhere at home is cool. But, I mean, I had a horrible Valentine's experience when I was single.

PS: Oh, what happened?Heather: I liked this guy, and he asked me out. And he said, "How about next Saturday?" which was Valentine's Day, so I was like, "That's great!" In the meantime, this other doctor that I went on a date with was, like, "Would you like to go on this dinner at this other doctor's house for Valentine's Day with me?" And I was, like, "I can't — I already made plans." You know, with this other guy. So then, the first guy calls me that Saturday and says, "What do you want to do? Where should we go?" And I said, "Well, it's Valentine's Day, so you know it's going to be hard to get into a place unless you made a reservation," and he's, like, "Oh, it is? I didn't know that."

PS: That's awful! How was the rest of the date?Heather: The guy picks me up — we go to a place. It's kind of like a Cheesecake Factory but not as nice, just like a whatever place. Then on the date, we're talking about stuff, and he says, "I hate the beach." I'm, like, "How do you hate the beach?" And I was, like, "Then we really should just end this date right here." I mean, we're never going to get married. We're never going to go on a honeymoon by the beach. Our kids are never going to frolic in the sand. And now I've wasted a precious Valentine's Day at like 27 years old, prime time for dating, on this guy who hates the beach.

PS: If you're dating a new guy, what should you get him for Valentine's Day?Heather: I think just something small. If you overdo it, you're going to look like a freak. If they're sleeping with them, I feel like they should get something for themselves like lingerie they can keep after the guy is gone. I wouldn't give them any gifts that they could take away with them. And then if it's really new, nothing too romantic — like a funny card and whatever guys like, like a cigar or a bottle of whiskey.

Group Therapy: I'm in the beginnings of what I think may be the last relationship I'll ever be in, and that thought scares me a bit. I don't believe in soul mates, but I do believe that two people can be perfect for each other in nearly every way. How do you know that your partner is the person you want to spend your life with?Heather: If it's easy — if you don't have to ever question if he's going to call you. If you don't ever have to try to figure out what his motives are. If you don't have to get on the phone with your girlfriend and analyze a text or a voice-mail message for an hour and a half like a CSI investigator, then that's a good relationship, and you shouldn't be afraid of it. If you get along, and it's easy, you should go for it. And you shouldn't be thinking is there something better out there, because you found it already.

GT: After having sex, I didn't really hear too much from him. He sent me a message later on, letting me know that he is overwhelmed and just feels out of sorts. I then asked him if he needed some space, to which he replied, "I don't know. I guess." I know sometimes guys say things so they can let down a woman gently. I'm wondering if this is a clear sign that I should move on or sit tight.Heather: It's definitely a "move on." That's a horrible story. I mean, isn't it? Yeah, don't text him anymore. Don't do anything. It's over. Who cares? You don't need to try to push and make something that it's not.

GT: I'm currently in a friends-with-benefits situation with a guy who is very much younger than me. This is the first time I've been in such a relationship. I was crushed when I realized that it was a friends-with-benefits arrangement because I had grown really attached to him. It gets worse, too, as he is also seeing other girls — all with similar arrangements. What should I do?Heather: Well, I would say it was OK, except but now she's falling for him, and she's going to get really hurt in the end. She should cut her losses and stop seeing him because it's just going to crush her even more. She's going to get more and more addicted to this relationship. She's going to get more hurt that he's not committed, and he doesn't want the same thing. And if she was being a friend of herself, like a friend came to her, she would tell the friend to stop seeing him. So she should be a friend of herself and cut her losses.